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CAS No. : | 4949-44-4 | MDL No. : | MFCD00009317 |
Formula : | C7H12O3 | Boiling Point : | - |
Linear Structure Formula : | C2H5C(O)CH2C(O)OC2H5 | InChI Key : | UDRCONFHWYGWFI-UHFFFAOYSA-N |
M.W : | 144.17 | Pubchem ID : | 78656 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With piperidine; acetic acid; In acetonitrile; at 80.0℃; for 4.0h; | Step A: A mixture of tert-butyl 4-(4-formyl-3-hydroxyphenyl)piperazine-l- carboxylate (3.0 g, 9.8 mmol, prepared in Example 1, Part 2), ethyl 3-oxopentanoate (1.62 mL, 11.3 mmol), AcOH (650 mu, 12 mmol), piperidine (1.1 mL, 11.3 mmol), and CH3CN (24 mL) were heated at 80 C for 4 h. The reaction mixture was partitioned between CH2CI2 and H2O. The organic layer was dried over MgS04, filtered, and concentrated under vacuum. The residue was purified by silica gel column chromatography (10%> EtOAc in CH2CI2), followed by ether trituration, yielding tert-butyl 4-(2-oxo-3-propionyl-2H-chromen-7-yl)piperazine-l-carboxylate (3.6 g, 95%) as a yellow solid. 1H NMR (500 MHz, CDC13): delta 8.49 (1H, s), 7.50 (1H, d, J= 8.5 Hz), 6.83 (1H, dd, J= 8.5 Hz, 2.5 Hz), 6.67 (1H, d, J= 2 Hz), 3.63 (4H, m), 3.47 (4H, m), 3.16 (2H, q, J= 7 Hz), 1.52 (9H, s), 1.19 (3H, t, J= 7 Hz). |
95% | With piperidine; acetic acid; In acetonitrile; at 80.0℃; for 4.0h; | Step A: A mixture of <strong>[1446332-69-9]tert-butyl 4-(4-formyl-3-hydroxyphenyl)piperazine-1-carboxylate</strong> (3.0 g, 9.8 mmol, prepared in Example 1, Part 2), ethyl 3-oxopentanoate (1.62 mL, 11.3 mmol), AcOH (650 muL, 12 mmol), piperidine (1.1 mL, 11.3 mmol), and CH3CN (24 mL) were heated at 80 C. for 4 h. The reaction mixture was partitioned between CH2Cl2 and H2O. The organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by silica gel column chromatography (10% EtOAc in CH2Cl2), followed by ether trituration, yielding tert-butyl 4-(2-oxo-3-propionyl-2H-chromen-7-yl)piperazine-1-carboxylate (3.6 g, 95%) as a yellow solid. 1H NMR (500 MHz, CDCl3): delta 8.49 (1H, s), 7.50 (1H, d, J=8.5 Hz), 6.83 (1H, dd, J=8.5 Hz, 2.5 Hz), 6.67 (1H, d, J=2 Hz), 3.63 (4H, m), 3.47 (4H, m), 3.16 (2H, q, J=7 Hz), 1.52 (9H, s), 1.19 (3H, t, J=7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With polyphosphoric acid; at 120℃; for 2.0h; | To a solution of 6-choro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (4 mL) was added ethyl 3-oxopentanoate {913 pL). The mixture was heated to 85 “C for 1 hour, then 120 C for 1 hour. While hot, the mixture was slowly transferred to a stirred solution of saturated aqueous NaHCC {~150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes then the organic layer was isolated. The aqueous layers was further extracted with chloroform/IPA (4:1) (x3) and the organic layers were pooled, dried over MgS04, filtered, and concentrated under vacuum. Upon cooling, a solid precipitate was observed. Hexanes was added, the suspenion was sonicated, the solid was collected by vacuum filtration, and washed with hexanes to provide the title compound (469 mg, 57% yield) >95% dean by LCMS. NMR (400 MHz, CDC ) d 6.50 (s, 1H), 2.70 (q, J 7.6 Hz, 2H), 2.61 (s,3H), 2.48 (s, 3H), 1.30 (?., J = 7.6 Hz, 3H). ES-MS [M+l]+: 238. |
57% | With polyphosphoric acid; at 120℃; for 2.0h; | To a solution of 6-choro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (4 mL) was added ethyl 3-oxopentanoate {913 pL). The mixture was heated to 85 “C for 1 hour, then 120 C for 1 hour. While hot, the mixture was slowly transferred to a stirred solution of saturated aqueous NaHCC {~150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes then the organic layer was isolated. The aqueous layers was further extracted with chloroform/IPA (4:1) (x3) and the organic layers were pooled, dried over MgS04, filtered, and concentrated under vacuum. Upon cooling, a solid precipitate was observed. Hexanes was added, the suspenion was sonicated, the solid was collected by vacuum filtration, and washed with hexanes to provide the title compound (469 mg, 57% yield) >95% dean by LCMS. NMR (400 MHz, CDC ) d 6.50 (s, 1H), 2.70 (q, J 7.6 Hz, 2H), 2.61 (s,3H), 2.48 (s, 3H), 1.30 (?., J = 7.6 Hz, 3H). ES-MS [M+l]+: 238. |
57% | With polyphosphoric acid; at 120℃; for 2.0h; | To a solution of 6-choro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (4 mL) was added ethyl 3-oxopentanoate {913 pL). The mixture was heated to 85 “C for 1 hour, then 120 C for 1 hour. While hot, the mixture was slowly transferred to a stirred solution of saturated aqueous NaHCC {~150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes then the organic layer was isolated. The aqueous layers was further extracted with chloroform/IPA (4:1) (x3) and the organic layers were pooled, dried over MgS04, filtered, and concentrated under vacuum. Upon cooling, a solid precipitate was observed. Hexanes was added, the suspenion was sonicated, the solid was collected by vacuum filtration, and washed with hexanes to provide the title compound (469 mg, 57% yield) >95% dean by LCMS. NMR (400 MHz, CDC ) d 6.50 (s, 1H), 2.70 (q, J 7.6 Hz, 2H), 2.61 (s,3H), 2.48 (s, 3H), 1.30 (?., J = 7.6 Hz, 3H). ES-MS [M+l]+: 238. |